4-bromothiophene-2-carbaldehyde oxime | 31767-01-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 4-bromothiophene-2-carbaldehyde oxime
• 英文别名: 4-Brom-thiophenaldehyd-(2)-oxim；4-Brom-2-thiophenaldehydoxim；4-bromo-2-thiophenecarboxaldehyde, oxime；4-Bromo-thiophene-2-carbaldehyde oxime；N-[(4-bromothiophen-2-yl)methylidene]hydroxylamine
• CAS: 31767-01-8
• 化学式: C₅H₄BrNOS
• mdl: MFCD00174330
• 分子量: 206.063
• InChiKey: PKYPVSRCCJULBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  4-bromothiophene-2-carbaldehyde oxime 在 乙酸酐 作用下， 生成 4-溴噻吩-2-腈
  参考文献：
  名称：

  Fournari,P. et al., Bulletin de la Societe Chimique de France, 1967, p. 4115 - 4120

  摘要：

  DOI：
• 作为产物：
  描述：

  4-溴-2-噻吩甲醛 在 盐酸羟胺 、 三乙胺 作用下， 生成 4-bromothiophene-2-carbaldehyde oxime
  参考文献：
  名称：

  Inhibition of IKK-2 by 2-[(aminocarbonyl)amino]-5-acetylenyl-3-thiophenecarboxamides

  摘要：

  A series of 21 novel 2-[(aminocarbonyl)amino]-5-acetylenyl-3-thiophenecarboxamides were synthesized and evaluated for the inhibition of IKK-2. In spite of their often modest activity on the enzyme, six selected analogs showed significant inhibition of the production of inflammatory cytokine IL-8 in IL-1 beta stimulated rheumatoid arthritis-derived synovial fibroblasts, demonstrating their potential usefulness as NF-kappa B regulators. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.090

文献信息

• Highly efficient synthesis of primary amides <i>via</i> aldoximes rearrangement in water under air atmosphere catalyzed by an ionic ruthenium pincer complex
  作者：Fa-Liu Yang、Xinju Zhu、Dun-Kang Rao、Xiao-Niu Cao、Ke Li、Yan Xu、Xin-Qi Hao、Mao-Ping Song

  DOI：10.1039/c6ra07515k

  日期：——

  aldoximes to primary amides has been evaluated using pincer ruthenium complexes a–c, among which the ionic Ru catalyst a proved to be the most efficient in water under air atmosphere. A variety of (hetero)arene aldoximes proceeded smoothly to afford amides in high yields with good functional group compatibilities. Furthermore, a direct synthetic route of amides from aldehydes, hydroxylamine hydrochloride

  使用夹钳式钌络合物a–c评估了醛肟肟向伯酰胺的转化，其中离子Ru催化剂a被证明在空气中在水中是最有效的。各种（杂）芳烃醛肟可顺利进行，以高收率提供具有良好官能团相容性的酰胺。此外，还描述了由醛，盐酸羟胺和碳酸钠直接合成酰胺的途径，其底物包括共轭醛和脂族醛。该方案操作简单，并以低催化剂负载量（0.5摩尔％）进行。
• Highly regioselective 1,3-dipolar cycloaddition of 3′-O-propargyl guanosine with nitrile oxide: An efficient method for the synthesis of guanosine containing isoxazole moiety
  作者：Muthian Shanmugasundaram、Annamalai Senthilvelan、Anilkumar R. Kore

  DOI：10.1016/j.tetlet.2020.152464

  日期：2020.10

  The 1,3-dipolar cycloaddition reaction of 3′-O-propargyl guanosine with various in-situ generated nitrile oxides in the presence of DMF as a solvent is described. It is noteworthy that the reaction is highly regioselective that affords biologically important guanosine containing isoxazole moiety in good yields with high purities.

  描述了在 DMF 作为溶剂的情况下，3'- O-炔丙基鸟苷与各种原位生成的氧化腈的 1,3-偶极环加成反应。值得注意的是，该反应具有高度区域选择性，能够以良好的收率和高纯度提供具有生物学重要意义的含有异恶唑部分的鸟苷。
• Synthesis, Identification, and Structure–Activity Relationship Analysis of GATA4 and NKX2-5 Protein–Protein Interaction Modulators
  作者：Mikael Jumppanen、Sini M. Kinnunen、Mika J. Välimäki、Virpi Talman、Samuli Auno、Tanja Bruun、Gustav Boije af Gennäs、Henri Xhaard、Ingo B. Aumüller、Heikki Ruskoaho、Jari Yli-Kauhaluoma

  DOI：10.1021/acs.jmedchem.9b01086

  日期：2019.9.12

  cytotoxicity. The structure-activity relationship (SAR) analysis revealed that the aromatic isoxazole substituent in the southern part regulates the inhibition of GATA4-NKX2-5 transcriptional synergy. Moreover, inhibition of GATA4 transcriptional activity correlated with the reduced cell viability. In summary, comprehensive SAR analysis accompanied by data analysis successfully identified potent and selective

  转录因子GATA4和NKX2-5直接相互作用并协同激活几种心脏基因和牵张诱导的心肌肥大。以前，我们将苯基异恶唑羧酰胺1确定为命中化合物，该化合物可抑制GATA4-NKX2-5转录协同作用。在此，通过合成和表征220个衍生物和与结构相关的化合物，探索了1分子结构周围的化学空间。除了协同转录激活，还评估了所选化合物对GATA4和NKX2-5转录活性的影响以及潜在的细胞毒性。结构-活性关系（SAR）分析表明，南部的芳族异恶唑取代基可调节对GATA4-NKX2-5转录协同的抑制作用。而且，对GATA4转录活性的抑制与细胞活力的降低有关。总之，综合的SAR分析和数据分析成功地确定了GATA4-NKX2-5转录协同作用的有效和选择性抑制剂，并揭示了对其重要的结构特征。
• Copper(II) Acetate-Catalysed Conversion of Aldoximes to Amides under Mild Conditions
  作者：Xiaoyun Ma、Ming Lu

  DOI：10.3184/174751916x14737790864571

  日期：2016.10

  A mild method for the metal-catalysed conversion of aldoximes to amides has been achieved by the combined use of copper(II) acetate and MeCN in EtOH under reflux. The presence of a catalytic amount of MeCN (0.05 equiv.) accelerated the reaction and improved the yield. Aryl, heteroaryl and alkyl aldoximes were transformed into the corresponding amides in moderate to good yield. 2-Furyl and 2-thiophenyl

  通过在 EtOH 中在回流下联合使用醋酸铜 (II) 和 MeCN，实现了一种将醛肟金属催化转化为酰胺的温和方法。催化量的 MeCN（0.05 当量）的存在加速了反应并提高了产率。芳基、杂芳基和烷基醛肟以中等至良好的产率转化为相应的酰胺。具有位于肟基邻位的杂原子孤对的 2-呋喃基和 2-噻吩醛肟显示出增强的反应性，并且以优异的产率获得了相应的酰胺。
• Discovery of Natural Rosin Derivatives Containing Oxime Ester Moieties as Potential Antifungal Agents to Control Tomato Gray Mold Caused by <i>Botrytis cinerea</i>
  作者：Yanqing Gao、Renle Xu、Shihao Gu、Kun Chen、Jian Li、Xiaohua He、Shibin Shang、Zhanqian Song、Jie Song

  DOI：10.1021/acs.jafc.2c01532

  日期：2022.5.11

  series of dehydroabietyl oxime ester derivatives were synthesized using rosin as a raw material. Based on the evaluation and screening of in vitro antifungal activities against Botrytis cinerea (B. cinerea), Sclerotinia sclerotiorum, Valsa mali, Rhizoctonia solani, Fusarium oxysporum, and Alternaria alternata, compound 4f exhibited the best antifungal activity against B. cinerea, and its EC50 was 0.798

  受天然产物抗病原真菌应用的启发，以松香为原料合成了两个系列的脱氢枞基肟酯衍生物。通过对灰霉病菌、核盘菌、马里瓦尔萨、立枯病菌、尖孢镰刀菌和链格孢菌体外抗真菌活性的评价和筛选，化合物4f对灰霉病菌的抗真菌活性最好，其欧共体50为0.798 mg/L，低于阳性对照品醚菌酯（1.112 mg/L）。体内抗真菌活性结果表明，4f对番茄具有满意的保护和疗效。生理生化研究表明，化合物4f对灰霉病菌的作用机制是改变菌丝体的形态和超微结构，增加细胞膜的通透性，引起细胞核和线粒体功能障碍，从而导致细胞凋亡。此外，定性和定量构效关系研究表明，化合物4f之间的诱导和共轭相互作用与靶受体形成电子转移过程，从而达到抗真菌作用。这些结果表明，衍生自天然产物松香的化合物4f是一种新的潜在的抗灰霉病菌候选物。